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Season 5: The Best of the Best Season 5 was when it all came together for The Simpsons as a series. The show was well established and could start taking risks, the running gags were still fresh, yet familiar, and the cast of characters was solidified in the collective consciousness of viewers. I'm going to make a bold statement: Season 5 is without a doubt the finest single season of The Simpsons ever made. Every show has its golden age. The Simpsons' started with season 4, peaked at season 5, and slowly trailed off in 6 and 7. Buy it, love it, live it! Homer for president!